Dennis Hopper would be a hoot, I think.
Louis Black.
Willie Nelson for the best weed.
Carly Simon because I’ve had a crush on her half my life.
Kurt Vonnegut before his death.
Whoopi Goldberg.
Warren and Jimmy Buffet
Good call. ('cuz, you know, after it just gets weird. Plus there is the smell.)
If we’re mentioning dead celebrities, I would pick Evan Hunter.
For live people, Steven & Tabitha King and their children.
Linda Lovelace and Marilyn Chambers would be fun.
But as far as people to sit next to on an airplane goes, pretty high on your list, right? 
My list:
Movies: Christopher Walken. Because he’s Christopher freaking Walken. Second place goes to Christian Bale, cause I want to talk to him about how he got cast in his different roles (I mean, this same guy was in Newsies and American Psycho, if that’s not wide acting range, I dunno what is)
TV: Either Richard Hatch or one of the Firefly cast members (Nathan Fillion, Adam Baldwin, and Adam Tudyk all strike me as hillarious, Jewel Staite is unbelievably cute, and I have a couple friends who would explode from envy if I got to hug Summer Glau) EDIT: On second thought, Paul Gross. That man is hilarious.
Music: Whoever it was who wrote the song that goes “Signs Signs, Everywhere are signs” I kinda want to whack him upside the head with a “No Trespassing” sign cause his uberpretentious song got stuck in my head for a week. Second place goes to Michelle Branch for being really cute, having really great songs, and apparently being a Pentax camera owner, judging by the jacket art for her “Hotel Paper” CD. Oh, and for singing a kickass duet with Sheryl Crow.
Trey Parker and Matt Stone. We’d have a great time making fun of everyone and everything.
Joss Whedon, for the awe-inspiring storytelling and geekery.
Tom Waits, for guaranteed bizarreness, amazing stories, and the saddest, most beautiful music in the world. (However, I’ve read enough interviews with him to know he’s a difficult guy to hang out and get along with.)
Ava Devine, Brittany Andrews, Taylor St. Claire, Mika Tan, and Kianna Dior, for obvious reasons.
Trying to pick people who haven’t already been chosen and staying on the fe/male designation, as best I can …
Movies: Pacino or Jenny McCarthy (I know, but still!)
TV: Chef Duff on “Ace of Cakes” or Rose McGowan (she used to be!)
Comic: Denis Leary or Whoopi
Music: Aerosmith or Marianne Faithful (badass enough to sing with Metallica, before they sold out IMHO)
Literature: Jack Ketchum or Poppy Z. Brite
Sports: Dirk Nowitzki (he’s way cool and I have a crush!) or Billie Jean King (Bobby Riggs – hehehehe)
Dead folk: Coolidge or Dorothy Parker
I’m all about teh funnaaaaay bay-bee!! 
Who would wanna hang out with anyone who takes themselves too seriously??
P.S. A Fie! on all those who beat me to Walken, Jackson, Winslet, Pink, Yogi and Laurie, plus Twain and Wilde. Darn y’all. Darn y’all all to heck!
I heard Vince Vaughn being interviewed on the radio once and I remember thinking “Hey! That guy’s just like us! He’s also funny and seems pretty cool”. I think I could hang out with Vince Vaughn.
Movies- Kevin Smith (down to earth, smart, and a total geek)
Music- David Gilmour (my idol, a brilliant guitarist, and seems laid-back)
TV- Danny Masterson (Hyde is the MAN)
Books- Stephen King (Dark Tower. 'nuff said)